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Born in Chatham, Kent,[4] Essam joined Gillingham in 2002 and progressed through the ranks of the youth team and also captained the side.[5] In March 2010, Essam was awarded his first professional contract along with Dean Rance and Charlie Stimson.[6] He was sent out to Conference South side Bishop's Stortford in October 2010 on an initial one-month loan which was later extended.[7] Later on in the season he joined Dover Athletic on loan in the same division.[8] In August 2011, Essam rejoined Bishop's Stortford of the Conference North on a one-month loan deal along with Dean Rance.[9] He scored his first goal for the club on 29 August in a 5–0 win over Hinckley United.[10] Essam joined Conference South outfit Dartford on loan in December 2011.[11] He scored in the 4–1 away league win over Staines Town.[12] Essam made his professional and Gillingham debut on 13 February 2012 in a 2–1 home defeat to Southend United.[13] On 31 August 2012 Essam signed for Luton Town on a month-long loan, later extended for a second month.[14][15] He returned to Gillingham on 2 November after making nine appearances for Luton, and was swiftly made available on a free transfer by Gillingham manager, Martin Allen.

On 27 July 2015, Essam signed for Football League Two side Leyton Orient. After a successful trial with the club he was offered a one-year contract. In May 2016, he was released from Leyton Orient when it was announced that he would not be retained when his contract expired.[18]

On 14 June 2016, Essam joined National League side Eastleigh on a one-year deal.[19] After only making five appearances in the space of a month, Essam joined Woking on a 93-day loan.[20] Two days later, Essam made his Woking debut in a 1–1 draw against Guiseley, playing the full 90 minutes.[21] However, just after a month into his loan spell with Woking, Essam was recalled by Eastleigh to cover an injury crisis.[22] After a short spell back at Eastleigh, Essam once again left the club on loan, this time returning to Dover Athletic on a deal for the remainder of the campaign.[23] Following a successful loan spell back at Dover, it was announced that Essam would leave Eastleigh in June 2017 upon the expiry of his current deal.[24]